Therapy Sessions
by Arsaem
Summary: It started out almost normal. All he was doing was counseling a guy with anxiety. Sure, the anxiety was caused by a ghost sickness, but that was just details. It only got worse from there. Suicidal teddy bears, an insane angel...and now, this. The Winchester's unofficial official therapist could really use therapy after this.
1. Chapter 1

**Obviously, I could use some therapy myself.**

* * *

 **Therapy Sessions**

Chess had really been hoping that he'd never see the Winchester brother's again. That he wouldn't ever have to deal with their craziness and danger and their horribly co-dependant relationship built on a broken childhood and traumatic experience after traumatic experience. Seriously, he could write a book on those two. Then again, no one would take something like that seriously. Chess wondered if he could psychoanalyze the brothers without including all the supernatural stuff, but he just didn't see it happening. Maybe he could write a psychological drama with demons and werewolves in it based on their lives. Except he really didn't think they'd appreciate that.

Chess was a shrink. The first time he met the Winchesters, he very quickly made it on their bad list by giving them a long list why they both should really get therapy, managing to guess all sorts of things about their lives just by observing their mannerisms towards one another and their overall behaviour (he was very good at what he did). He vaguely managed to redeem himself when he later helped them defeat the ghost by talking her into moving on into...wherever ghosts go. It was just a simple case of extreme OCD and ICD (impulse control disorder). So extreme that the lady actually stuck around after she kicked the bucket. Fortunately, therapy is much easier when all you have to do is convince the person that it's time to move on, even if the canned goods weren't stored just right.

Chess wasn't expecting to hear from the Winchester's ever again. But then a thing happened, something to do with a ghost and some kind of magical sickness and now Dean had anxiety. Like, really serious anxiety. And it was only going to get worse. It was Chess' job to keep him calm and relaxed so that he didn't literally die of fright while Sam took care of the ghost. Easier said than done, when you have a full-grown man frightened of his own shadow.

"Just stay calm, Dean" Chess told him soothingly. "You understand the situation. The fear isn't real. It's just the, uh, ghost sickness. There is literally absolutely nothing to be afraid of."

"You think I don't know that!" Dean shouted back. "It's freakin' ridiculous! Really! But y'know what, I really _do_ have something to be afraid of! I mean, first of all, Sam and I hunt monsters! Who does that? Actual, live monsters! That can kill us! And then there's that whole thing with heaven and hell and God-damned Lucifer rising and angels telling me I gotta go do stuff and I have to do it because they pulled me from hell and I just don't! Okay, I don't!"

Chess tried to keep a neutral face. He had a vague idea of what happened, something about angels rising Dean from hell and seals breaking and the upcoming apocalypse. Chess had been planning on moving to Rome.

"Well, why don't you tell me about that," Chess told him. "The angels, what do you feel about them?"

"Eh, not much, just that they're dicks," Dean replied. "Well, I mean, I've only met Castiel, and he _did_ save me from hell, but that guy is freakin' weird. He took me back in time to when my mom's parents were murdered! By the same demon that killed her and my dad! And I couldn't do anything to stop it!"

Well, this was new. Chess had certainly worked with people who've lost one or both their parents, in every way possible. He's never had to deal with a guy who had to face his parents...after they both were dead...back before he was even conceived in his mom's womb. How do you approach that? Dean was hyperventilating though, so Chess didn't have time to figure out an answer.

"Deep breaths," he instructed. "In through the nose, out through the mouth. That's it, breathe deep. It's okay Dean. Sam is taking care of it right now." He decided to put the therapy session on hold and instead do what he had been instructed to do: keep Dean calm. "I want you to think about your happiest memory," he said, nodding in satisfaction when he saw that Dean at least had his breathing under control. "Close your eyes, and picture that moment." Dean did as he was instructed, and Chess spoke again. "Can you tell me what you see?"

"I'm with Sam," Dean replied. That was a given. It it didn't have Sam in it then it wasn't a happy memory. Dear God those two have problems. "It's Fourth of July. Dad was out on a hunt. Just me and him. I stole some fireworks and took Sam out to a field where we lit them up. Sam was so excited" For a moment, Dean had a little smile on his face. But then his eyes screwed up and he shuddered. "Oh my God we could've burned the whole field down! We were lighting them and holding them in our hands! We could've died! We-"

"Dean!" Chess broke in, prompting his eyes to shoot open and look at him with uncontrolled fear. "This is a memory. Nobody got hurt. The field didn't burn down." Crap, he may have just ruined one of Dean's best memories. "There's nothing to fear. You and Sam had a great time, and nobody got hurt," he repeated, firmly. "Deep breaths," he reminded. If Sam didn't hurry this up then _he_ was going to go insane.

This went on for about another twenty minutes, and Chess was at his wits end, until finally, _finally,_ whatever magic spell was over Dean suddenly broke, and he was back to his usual, obnoxious self, albeit looking quite embarrassed.

After is was all over, Chess made the mistake of sticking around. He wanted to learn a bit more about this whole 'ghost sickness' thing and how it affected a person's mental health. He stuck with Bobby, reading ancient texts and old lore while Halloween was almost ruined by a couple of witches summoning a _really bad demon._ After a charming explanation of what a dick the angel Uriel is, Chess finally decided to head home and hitched a ride with the Winchester's, since they were heading in the same general direction anyway. That's when he became a teddy bear's therapist.

"You've got to be kidding me," he groaned, because really, ghosts are one thing, but a giant, anthropomorphic, talking _teddy bear?_ Not even to go into the major depression disorder, anxiety, catastrophic thinking, oh, and _thoughts of suicide._ He was dealing with a suicidal teddy bear. A teddy bear who was contemplating ending his fluffy existence, once and for all. Chess was beginning to think _he_ needed therapy. Right after the Winchesters.

"So...um…" Chess was trying, he really was, but he honestly didn't know what he was supposed to do with a depressed teddy bear. And OH GOD WHERE DID HE GET A GUN!

"Hey, whoa there, let's, uh, let's not do anything hasty!" Chess quickly tried to talk him down. He was trying to talk down a teddy bear. With a gun. Did he mention it was a freakin' teddy bear?!

"There is no hope," the bear groaned dramatically. "No way to drown out the sorrow!" Obviously, the copious amounts of alcohol it consumed hadn't helped. Where it even went, Chess didn't want to know. It had also smoked through two packets of cigarettes, which made Chess wonder how it did that if it didn't have breath. Did it have breath? "I should just end it now, do the world a favor," the bear murmured, putting the gun under its chin.

"Hey, the world ain't so bad," Chess told him, trying for a smile, immensely relieved that the gun wasn't for him. "That girl, Audrey, really cares about you, y'know." This...this was weird. Even by Winchester standards this was weird.

"Yes," the bear admitted. "But not for long. I know how these things work! Soon, all Audrey will care about is makeup and boys and I'll just end up in the dump! I saw Toy Story, you know!" The bear started sobbing again. "There's nothing to live for! The world is full of horror and terror, and there's just no room for a teddy bear anymore!" Chess had to contemplate if he wanted to scream or not when the gun fired, blowing a hole in the bear's head and sending fluff everywhere. But then the bear moved and his sobs continued, as he discovered that not even death could give him release.

"W-well, um...yeah," Chess murmured shakily. He reached out slowly and gently gripped the gun. "Why don't we just put that down...yep, nice and calm, everyone's fine…" Chess managed to get the gun away and set it carefully on the ground. "Let's just take it easy," he said. "Y'know, Sam and Dean are fixing the problem right now. You'll go back to being a normal teddy bear, and then this will all be over." Chess wondered if this technically counted as encouraging suicide. But he was currently talking to a teddy bear who just blew his brain-fluff out, so he figured this was allowed. At this point, the only thing that would actually help this bear would be to cease to exist.

Chess wasn't completely heartless, however, so found needle and thread and went to work fixing the bear's head, ignoring it when it told him to just leave it. And, since Chess was feeling particularly bored, he even collected all the brain-fuzz and shoved it back where it belonged. The stitches were a bit sloppy, and he hadn't used thread that even remotely matched the bear's fur (to be fair, bright yellow just happened to be the first spool he grabbed) so it really stuck out, but at least the bear wasn't spilling its brains everywhere. It wasn't long after that that the teddy abruptly shrank and turned into a normal, inanimate, stuffed creature. With bright yellow stitching on its head. Chess ditched the Winchesters very soon after that.

-0-

Chess had tried to avoid the Winchesters. He really did. But when Dean called spouting some nonsense about how he had to "come fix Sam because he's hallucinating Satan and literally driving him crazy…" Well, he couldn't _really_ say no. For starters, they did save his life. And besides, Sam hallucinating the devil? And most likely the actual devil, seeing how they fought him not too long ago…

Chess needed to find different friends.

By the time Chess made his way to the correct hospital, Sam was all better, and now he had a crazy angel to deal with. Yep. And angel. Honest-to-God, real life angel. Of course, Chess had heard about them in passing from the Winchester brothers, but he didn't think he'd ever actually _meet_ one.

Much less an insane one.

It was easy enough to get hired to the facility, and after some careful maneuvering, Chess suddenly found himself abandoning his old life and home to watch and -hopefully- fix a crazy angel with a demon as backup. Yep, his nurse was a demon.

Talking to Castiel was...interesting. Mostly because he got no response. The first three weeks consisted of annoying remarks from 'Meg.'

"What were your parents thinking when they named you?" she snarked. "Seriously, who names their kid Chess?"

"It's a nickname," he told her through gritted teeth. "My real name is Chris." He'd been going by Chess for so long that he didn't even bother with trying to go by anything else. He got the nickname after proving himself to be the supreme-nerd-master at chess in his sophomore year of his high school's chess competition. Not that he was going to tell Meg that.

"Mn, okay then Chrissy," she told him with a smirk.

"Don't call me that."

"Sure thing Chrissy." She grinned at him, and he glared. Castiel stared blankly at the wall. And then he blinked. It shouldn't have been that big of a deal, but the angel had not blinked for three weeks straight. At least, not on his own. In order to ward away suspicion, Chess and Meg laid Castiel down every night and closed his eyes to make it look like he slept. They also brought him food, but Chess was always the one who ate it.

"Castiel?" Chess spoke softly, hoping to get the angel's attention. "Castiel, can you hear me?"

Slowly, ever so slowly, Castiel moved his head half an inch, and looked at him. Chess let a small smile appear, but nothing more. He didn't want to appear too excited.

"Castiel, do you know who I am?" Chess asked next. "I introduced myself earlier, but you seemed a little out of it. I'm Dr. Carnes, but you can just call me Chess. I'm a friend of Sam and Dean. Do you know who Sam and Dean are?"

Castiel stared at him. And then, a single, breathless whisper. "Lucifer."

"Do you see Lucifer?" Chess asked him softly. "Do you see me as Lucifer? Castiel, I want you to understand this: I will never, _ever_ hurt you. I just want to help."

Castiel lifted his chin hardly a millimeter, but it was probably the closest to a nod he was going to get. And then he went back to staring at the wall.

Chess didn't get another response from him for another month, and it was a very alarming response, resulting in Castiel blowing out the lights every other hour. On the other hand, he was much more chatty now, and Chess finally had something to work with.

"Do you still see Lucifer?" Chess asked him gently. He was using the time it was taking the Winchesters to get here to do as much as he could to untangle the angel's messed up mind. Maybe he could do some good.

"Lucifer's my brother," Castiel told him, very seriously. "I loved him very much. He was the most beautiful angel, you know. I was still a fledgling when he fell. He taught me how to fly."

"O...kay." The problem was, Chess knew full well that Castiel wasn't hallucinating or lying or creating some false-reality for himself. This just wasn't someone being crazy. This was a case of a lost, young angel who loved his brother very deeply, before he was cast into the pits of hell, and then, centuries later, being cast out from his family as well, not to mention all the smiting and god-complex stuff that Sam and Dean told him about. And this was _before_ Castiel took Sam's crazy for himself. Chess mentally added Cas to the list of people who could really use therapy. At the moment, it consisted only of the Winchester brothers, and now him. Oh, and Chess himself as well, but that was neither here nor there.

"Let's talk about your family," Chess decided, since that seemed to be the bulk of the problem. "Can you tell me what it was like in heaven?"

"Well, I'm one of the youngest angels, you know. The very last to be created. I might even _be_ the youngest, I don't know," Castiel explained to him. "Anael took care of me and the other fledglings who would one day be in her garrison. But Lucifer and Gabriel would play with us a lot. Lucifer taught me how to fly. He threw me off a cliff and I learned how. Gabriel was really angry after."

"Were there any angels your were particularly close with?" Chess asked.

Castiel nodded. "Uriel. And Samandriel. Uriel…" He frowned, looked extremely upset. "He was helping break the seals. He was killing angels. He-" Castiel's eyes welled up with tears. "Anael killed him. He was trying to kill me, when I wouldn't join him. I loved him."

"I'm very sorry that had to happen," Chess told him sympathetically. This mess just got worse and worse. "Why don't you tell me about Samandriel then?"

Castiel nodded and wiped his eyes. "Samandriel and I used to play pranks on the other fledglings. This was before we started training to be soldiers, of course. Sometimes, Gabriel or Lucifer would help us. One time, Michael intervened. He was very displeased. That was the first time I met him. I never met Raphael until he killed me."

Right. Sam and Dean mentioned that Castiel had died. Twice. (Though, to be fair, it wasn't nearly as many times as Sam or Dean. In fact, according to Sam, Dean's died over a hundred times)

"Stay focused on Samandriel," Chess instructed him. There were too many bad memories in Castiel's head. He needed to help filter them before they could tackle them directly. "You and him were close?"

Castiel nodded. "He liked to tell human jokes. I never understood them."

Very quickly, Chess discovered his problem: Castiel wasn't exactly insane. Sure, he had one hell of a childhood, a really messed up family, and so many traumatic events that by all rights he should be on the floor, sniveling and crying. Except Castiel was an angel. Angels worked differently from humans. Sure, Castiel had a dark past, but he didn't take like a human would. He took it like an angel would. So, no, Castiel wasn't really insane. The insanity was just a side-effect of Sam's crazy. And Chess had no idea how to help with that.

It wasn't a normal mental illness. It had no rhyme or reason, and Chess wasn't even sure how to classify Castiel's behaviour now. Mostly just loopy. He really like bees for some reason. It was exhausting trying to figure anything out about the angel, and when the Winchesters finally arrived, Chess had nothing. He was also done. He packed up his things and went home, leaving the brothers with a stern warning to never contact him again. Chess thought it was finally all over…

-0-

Thinking back, Chess still couldn't decide which one was weirder: being a therapist for a suicidal teddy bear, or being a therapist for an insane angel. The teddy bear was, well, a _teddy bear,_ but at the same time, the angel was an _angel._ Both were completely and utterly ridiculous in their own right, but Chess could never decide which one was crazier.

This, however, definitely took the cake.

The Winchesters called again. Chess wanted to run away. But it sounded urgent. " _Your skills as a therapist might actually decide the fate of the world,"_ were Sam's exact words. Dean said something along the lines of, " _If this gets screwed up then everyone's screwed."_ So Chess supposed, for the good of humanity, he'd jump back into the game one last time.

And that was how he found himself conducting a therapy session between (drumroll please) _God and Lucifer._ The fact that he had to coax Lucifer out of a locked room that was blasting angsty, teenage music did not help. The fact that God insisted he call him 'Chuck' was like the cherry on top. Chess could almost, _almost_ imagine that this was a normal session. Except that their topic of discussion was how Chuck cast Lucifer from heaven into the fiery pits of hell for disobeying. Fun times.

"I hate you guys," Chess murmured to the Winchesters, and only got a cheeky grin and a slap on the back in response. Chess found himself asking _Lucifer,_ "How does that make you feel?" while asking _God_ if he, "Was maybe a bit too harsh?" and that he, "Should try to see the situation from, uh, Lucifer's point of view." The fact that each character got all smug and triumphant whenever Chess even mildly agreed with them was just another headache.

Finally, after an hour of arguing that just went in circles, Chess finally managed to get somewhere. Chuck admitted that he shouldn't have disappeared and should have listened better to his children. Lucifer admitted he may have overreacted just a teany bit, and also apologized for killing Gabriel. He added a moment later that Castiel also said he was sorry for killing Raphael and Balthazar and for opening Purgatory. Oh right. Lucifer was also, currently, _possessing Castiel._ Chess decided to deal with that one later.

"Lose my number," Chess informed the Winchesters when he finally left. "I'm serious this time." He didn't care if the freakin' world was about to implode, he was done with all this.


	2. Chapter 2

**Because God and Amara definitely have billions of years of issues to work out. And Chess and Lucifer are totally going to be best buds.**

* * *

 **Therapy With The Devil  
** **(Literally)**

It wasn't actually the Winchesters, this time, who dragged him back into things. But Chess still blamed them, because he was about 90% certain that he could trace back all the world's problems to a Winchester. He had decided that it was just easier to blame them for everything. But this was _definitely_ their fault. Because, apparently, Chuck (God, in case you forgot) thought that he was a pretty good shrink (from his one session he had...with Lucifer) and decided that he and his sister (yes, God's literal sister) needed to work through billions of years of issues. And Chess was their guy for the job (and here, you would insert any number of words of your choice, most of them four letters and to be repeated several times for effect).

Chess started his session with a glass of scotch. He swished the drink around miserably, wondering if he would get utterly obliterated if he decided to refuse God and his sister therapy, before heaving a monumental sigh and clicking his pen. Chuck had mentioned that he wanted this to become a regular thing, so he was taking notes. Didn't want to mess up and start the fifth (or was it sixth?) apocalypse.

"I just want you two to understand," Chess started, "that for this to work, you both are going to have to be open and willing to listen." God's sister (the Darkness, also known as Amara) nodded carefully. She looked uncomfortable. She also had a really low neckline. Chess was going to hell.

"I think we should start at the beginning," Chuck said, turning to his sister. "That's where everything fell apart, really."

Amara nodded. "I really want to forgive you, brother, but what you did to me still burns within me. First, it seemed that I was not enough for you. And then you locked me away and…" She was looking less on the angry and vengeful side and more on the hurt and alone side. Considering the fact that she nearly destroyed the sun a few weeks ago, Chess was more than willing to take hurt and alone over angry and vengeful.

"I'm sorry," Chuck answered. "I really am. It's just, you kept destroying everything I created. I know that's no excuse, but-" He gave a helpless shrug.

"You both had your reasons for what you did," Chess spoke up. "Maybe they weren't the best solution, but it's important to keep in mind that neither of you ever did something out of spite or hatred of the other." Chess was a little hesitant to intervene, since he really didn't want to get obliterated today, but he was holding on to the hope that Chuck was a nice-ish guy and wouldn't kill him without reason.

The therapy lasted for two hours before Chess finally cut in and said that they needed to take some time apart to think about what they've learned. Otherwise, they'll get nowhere (and, eventually one of them would get so upset and decide to blow something up). Amara didn't want to come back, but Chuck said it would be a good idea and nudged at Chess to help him. Crap.

"Well, um, continual therapy can really help your relationship and ensure that you don't inadvertently hurt each other again," Chess managed to spill out, all while wondering why he was encouraging the all-powerful beings to come back. Then again, God himself was asking him to do this. This really felt like a lose-lose situation, at least in Chess' case.

"Very well," Amara huffed. "We will return."

"Great!" Chuck sounded a little too forced in his cheer. "Next week, same time?" he asked, and Chess nodded wearily. Looks like his Wednesday's nights were now permanently taken.

"I'll see you two then," he told the pair, getting up to show them to the door when he blinked and suddenly they were gone. Well then…

-0-

Chess was trying to get a job. At the moment, he was something of a freelance therapist, since he had to quit his last job to go take care of an insane angel (he left that place after said angel left). He lost a lot of clients (not that he had that many to begin with) after suddenly taking off for two weeks in order to provide counseling to God and Lucifer (that will always sound crazy). And then Chess actually lost his license when he went in for an evaluation, and he was deemed just a tad too unstable (it wasn't _his_ fault that he was once a teddy bear doctor, nor was it his fault that he couldn't hide the effect the supernatural world had on him very well). But Chess still liked listening to people's problems, so he did the next best thing: became a bartender. As cliche as that sounds. Funny enough, it was bartending that first made him want to be a psychiatrist. Go figure.

So Chess was a bartender now, and he blamed Sam and Dean (as he always does), when he got a very unusual customer. Besides the fact that Chess was pretty sure he was some famous singer or something like that, he also walked right up to him and said, "Monday. Three o'clock. Dad said I had to do this." And then he left. It wasn't until Monday that Chess learned that he was actually Lucifer, and Chuck was basically forcing him to go to therapy. Fun.

So, Chess loses license, Chess suddenly gets big-name clients like God and Lucifer and God's sister. Go figure (again).

Lucifer wasn't very talkative. He sat on Chess' couch and just glared for a good twenty minutes, with Chess pushed as far back as he could in his chair, hoping to remain invisible. Chuck wasn't here to make sure he didn't get obliterated, so he was just a tad nervous.

"So-"

"Let me make one thing clear," Lucifer snarled. "I don't want to be here, I think this is a waste of time, and the only reason why I'm doing this is because Dad threatened to throw me back in the cage if I didn't. So what's gonna happen is that you're going to tell my father that everything went great, and that'll be the end of it."

Chess nodded, except he knew it wasn't (the end of it, that is). He was about 86% certain that Chuck could read minds, and he really didn't want to get on the guy's bad side by not giving the devil therapy. So, taking a deep breath, Chess steeled himself.

"I get it," he answered. "But, it is kinda boring to just sit here for two hours, doing nothing."

"So, what, you wanna talk about my 'feelings?'" Lucifer snarked, using air quotations on the last word.

"I mean, I'd rather not." And that was the honest truth. "We could talk about whatever you want. Or we could play a board game or something." Chess has dealt with tough clients before. Why was Satan any different?

"Well, I guess I wouldn't mind a game." He looked a bit embarrassed when he added, "I am a bit fond of, um...battleship."

"Fine by me," Chess answered, getting up to get the game. Hesitating slightly, he added in an extremely careful tone, "Just, uh, don't use any angel powers to cheat, because, y'know...that'd be boring."

Chess was certain he was going to get smote then and there. But then Lucifer just rolled his eyes and grumbled, "Fine."

Lucifer still won, but that came as something of a relief since Chess _really_ didn't want to see what would happen if he lost. By the second game, Lucifer started talking a bit, not really saying anything of importance, but it was a start.

"See, I don't get why you can't put the ships diagonal," Lucifer complained. "In real life, you can make ships go diagonal!"

"I think it's just because the pegs wouldn't really fit diagonal," Chess answered, because it seemed like the safest reply that was least likely to get him killed.

"It's still a stupid rule," Lucifer grumbled. "Y'know, the Bible has a lot of stupid rules. I mean, have you read Genesis? All those super exact details on how to light candles, and how to build your church, how to jump on one foot and sing the national anthem. Now, I don't know exactly what happened since it was after my time, but I'm pretty sure that Gabriel was just getting a good laugh when he told the guy what to write. I'm also fairly certain that every prophet who's ever lived went through life drunk or higher than a kite. Ridiculous." He shook his head. "And what's with all the 'Thou dost be-eth a prophet-eth?' I can't say the same for all my siblings, but I, at least, have _never_ talked like that."

Chess didn't say much, just nodded along and said what was necessary. All-in-all, not that bad for a therapy session with Lucifer. And whoa did that sound like the title to some angsty, teenage drama.

"So," Lucifer said once their time was up. Chess was packing away the game after losing for the fifth time in a row. "Same time next week, I guess. Don't want Dad getting on my back for not going."

"Yep," Chess squeaked, not even looking up when Lucifer was gone with nothing but a faint whooshing sound. Whoosh!

-0-

"So on Monday's you play board games with Lucifer, and on Wednesdays you counsel God and his sister?" Dammit, Chess knew he shouldn't have gotten drunk.

"Yep," he slurred, staring at his half-empty glass of beer. Jack, his friend, was looking at him with a worried look on his face. "Iss all tha Wi-chessers' fault," he grumbled. "Teddy bear doctor," he snorted. "An' uh insane angel! He liked bees…"

"Chess," Jack said uncertainly. "Is this some kind of nervous breakdown?"

Chess downed the rest of his beer and called over the waitress for another. "Nah. But Dean once hadda one, sorta. Ghost sickness. 'Fraid of his ohn' shadow." He gave a snorted laugh. "Stoopid…"

"Alright buddy, I'm taking you home," Jack said, taking away the fresh glass of beer and helping his friend up. He slapped down a few bills on the table and hurried them out, careful to strap the incoherent Chess into the passenger seat before buckling himself in. Chess kept muttering about the apocalypse and a demon named Meg, and Jack was getting seriously worried. Maybe listening to other people's problems all day had finally broke him.

Chess was wholly uncooperative in getting himself out of the car and into his house. It didn't help that Jack had to fish his keys out of his pocket, made extremely difficult when the guy wouldn't stop swaying. Jack almost just let his friend fall on the floor, but instead sighed and led Chess to the couch, flopping him down and setting his legs up. He grabbed a blanket and threw it over the now very asleep Chess, and set a trashcan next to him just in case. Jack was just about to leave when the phone rang. He supposed he could take down a message for Chess while he was here…

"Hello?"

"Chess? It's me, Sam. I know you wanted us to never contact you again, but this is important."

"Um, actually-"

"Look, Amara -you know, God's sister- raised our mom back to life, and she's having trouble adjusting. Would you mind just seeing her? Dean and I aren't really good at this stuff, and you are, and we'll pay you, I swear-"

"This isn't Chess," Jack cut in, because this call was getting _weird._ "Uh, I'm his friend, Jack. Chess is-" He glanced down at his sleeping friend. "-indisposed. What were you saying about your mom being raised from the dead by God's sister?"

Silence. And then, "Shit."


	3. Chapter 3

**Oh man it has a plot now. Sorta... Anyway, it looks like I'm going to be continuing this. I have another few ideas. Also, I'm really getting to like Lucifer's therapy sessions.**

* * *

 **Monopoly Night**

Chess didn't wake up till noon. And even then, he was completely fine with lying in bed for another hour or so. He never did hold his liquor all that well, nor was he all that great at hangovers. For a bartender, he kind of sucked at alcohol.

Unfortunately, Chess wasn't alone. It looked like Jack decided to stay the night...for whatever reason. He was in the kitchen, making an absolute ruckus with all his walking around and putting a pot of coffee on. Don't even get him started on the noise from the coffee machine. If it made one more drip sound, Chess just might throw it against the wall.

Except that his head was throbbing, and all he wanted to do was sleep for a week.

"Finally up?" Jack said, coming back into the living room. Chess might've thought it a little weird that he was on the couch instead of his bed, but he honestly didn't care.

"What're you doing 'ere?" Chess mumbled, forcing himself to sit up. He rubbed at his face tiredly, eyes sunken in, hair a complete mess.

"Well, I _was_ going to go home after I dropped you off here," Jack told him. "But, uh. Well, for starters, you said some really interesting things last night."

"Shit," Chess muttered, just to himself.

"And then some guy named Sam called-"

"Shit."

"-talking about how God's sister raised his mother from the dead."

"Shit."

"So, at the very least, I'm curious," Jack ended. "But I'm also concerned, and possibly freaked out, but I'm not sure yet."

"Shit." Chess rubbed his forehead and looked up at his friend. "Coffee?" he mumbled, prompting a sigh as Jack stood to get him a mug.

"Seriously dude, what's going on with you?" Jack asked when he came back, two coffee's in hand.

"I've become a supernatural therapist," Chess muttered to himself, sipping the hot liquid slowly. It burned his tongue and throat going down and he set it down to let it cool. Jack was still waiting for an explanation, so he looked up and said, "You wouldn't believe me if I told you."

"C'mon, we've been friends since high school," Jack reminded him. "What's going on?"

Chess rubbed at his eyes. "Okay. What, exactly, did I say last night?"

Jack shrugged. "Some real crazy stuff. Like, you have counseling sessions with God and his sister, and you like to play board games with Satan. And then there was that Sam guy talking about his recently brought back to life mom."

"Um...it's Sam," Chess muttered wearily in reply. "He's a client. Got some really crazy stuff going on in his head."

"Chess, your license was revoked last month," Jack reminded him.

A pause. "Right," Chess agreed after a moment. "When I say client, I mean that he's the brother of a friend of mine and I'm doing this as a favor, not getting paid."

"Really." Jack did not sound remotely convinced. "You never mentioned a Sam once last night." Thankfully, he left out the part where it was kind of illegal to be giving therapy to a guy without a license.

"Yep. I'm a weirdo. Can't hold my alcohol. No got away. I wanna sleep." Chess then stumbled to his room, fully intending to do just that. Jack, still worried that he might need to be admitted to a mental hospital, stuck around. Chess completely forgot it was Monday.

-0-

The silver lining was that Lucifer was no longer wearing the face of that singer guy. Chess never really learned his name, but apparently Chuck was a fan so he made Lucifer an extra-durable strength vessel who looked like the guy he was possessing when the apocalypse was still on. It was weird, to think that Chess has now seen Lucifer with three different faces (Castiel, singer guy, and now previous-vessel guy). It was also weird to think that God was a fan of some random rock band. But, at least Jack wasn't wondering why some famous singer decided to pop in on Chess at three o'clock sharp. And by pop in, he meant appearing out of thin air and nearly giving his best friend a heart attack.

"Well this is interesting," Lucifer commented once Jack had finished screaming. He turned to Chess and accused, "You forget about our appointment?"

"Would you smite me if I did?" Chess asked him wearily. He wasn't really all that concerned about Lucifer hurting him. As weird as it sounds, the devil wasn't so bad. So long as all they were doing was just playing board games and letting the conversation go where it may.

"I could, but I'm pretty sure my father would just bring you back," Lucifer replied, settling himself on the couch.

Jack was sitting in one of the plush chairs, hand clutched to his chest, eyes widened and staring at Lucifer. "On Monday's you play board games with Satan…" he mumbled.

"Hey, we don't use words like that anymore," Chess scolded him. "His name is Lucifer. Or Samael, if you really want."

Lucifer shrugged. "I'm fine with either one."

"You appeared out of nowhere," Jack breathed.

"Well, actually I _flew_ in, but your mortal mind could not even begin to comprehend something as majestic as my wings, so-"

"Alright, that's enough," Chess cut in before things could get out of hand. He turned to Jack. "You should probably go."

"No, no, let him stay!" Lucifer said. "With him here, we can play something that you need more than two people for. Like Monopoly!"

"Monopoly with Lucifer," Chess mused to himself. Yep. That was one way to die.

"Um…" Jack stuttered. "I...uh, um…" He looked at Chess helplessly.

"Would you like any further proof that this is Lucifer?" Chess asked him. "He could, I don't know, zap us to Rome. Or snap us a hot tub." He turned to Lucifer and asked, "Oh, could you snap my headache away?" Lucifer snapped his fingers. Chess' headache was suddenly gone. "Thanks," he said, sitting down in the other chair.

Lucifer nodded and turned to Jack. "Now then. You'll stay for Monopoly, right?"

And that was how they ended up playing Monopoly with the devil. Jack...did alright. His hands shook every time he rolled the dice, and Chess sensed a long conversation in their future, but all things considered, he did alright.

An hour later, Lucifer had boardwalk. Chess was doing okay with the pinks and the reds, and Jack was hanging on by a thread with just the oranges. Chess was 86% sure that Lucifer wouldn't smite anybody if he lost, and about 92% sure that Chuck would just bring them back if he did, but he still made sure that he and Jack ended up losing. Monopoly was, after all, the game that destroyed lives. And when you're playing with an all-powerful archangel who almost destroyed the world once…

"Ah, crap, I gotta call Sam!" Chess suddenly remembered, pulling out his phone. Jack looked up from his negotiations with Lucifer, trying to get possession of the last yellow. "He's probably freaking out after talking to you!"

"So, um…" Jack looked extremely uncomfortable. "God's sister bringing their dead mother back to life?"

"If it makes you feel any better, I once counseled a giant, talking, suicidal teddy bear." How that was supposed to make Jack feel better was anyone's guess, but Chess liked to bring up the teddy bear whenever he could. Because it was a GIANT, TALKING, SUICIDAL TEDDY BEAR.

"Hello, uh, Sam?" Chess said once he heard the phone being answered. "Yeah, sorry about what happened yesterday. Long story. I might have been drunk. And you don't need to worry about my friend, I've got it taken care of. So what's this I hear about your mom coming back to life?"

"Can I talk to Sam?" Lucifer asked, leaning forward, reaching for the phone.

"Uh-huh," Chess said into the phone, swatting his hand away. "Oh, wow. That's weird."

"I wanna talk to Sam!" Lucifer whined, this time grabbing at his arm.

"Well, y'know, your freak show's followed me home," Chess said, standing up and moving away, prompting a huff from Lucifer. "Yeah, on Wednesdays I have a session with Chuck and Amara. She never mentioned your mom. Oh, and I also have Chuck-ordained sessions with Lucifer on Mondays. Right now, actually." A pause. "No, no, it's fine. My friend Jack is here. We're playing Monopoly."

"Let me talk to Sam!" Lucifer all but demanded, standing up and stalking towards him.

"No, he hasn't tried to smite me. Anyways, Thursdays sound good? Two o'clock? And you _will_ pay me, right?" Chess waited for the answer and nodded. "Good. Oh, Lucifer wants to talk to you."

You could just hear the cries of alarm, something along the lines of, "Don't put Lucifer on!" when Chess handed over the phone. Okay, maybe that was a bad move, but he was still trying to avoid getting smote here.

"Sammy-boy!" Lucifer said into the phone cheerfully. "Guess who it is!" There was a muffled shout on the other line and he frowned. "Well, that's not a very nice thing to say!" More shouting. "Now, now, I'm done with the whole apocalypse thing. Dad's even trying to reform me, sending me to this human therapist guy. And, y'know, maybe-" He abruptly cut off and pulled the phone away from his ear. "He hung up on me!" he grumbled angrily.

Chess snatched the phone away and returned it to his pocket. Jack was white-faced with wide eyes. He had only just barely started to remotely get used to the whole Lucifer thing. God and his sister? People back from the dead? A whole 'nother can of worms. Also, it looked like Chess had another client.

* * *

 **Up next: Mummy dearest is back from the dead (pun fully intended)**


	4. Chapter 4

**You've probably noticed this by now, but I've tried to keep light on the actual therapy stuff. I have no experience or knowledge about psychology or the human mind, and I don't take this story seriously enough to research for it. So, don't take any of Chess' shrink-stuff to heart.**

 **On another note, Happy Thanksgiving! Didja eat lots of turkey and stuffing and mashed 'taters and pie? 'Cause I did! And for those of you who don't live in America...Happy Thursday? You guys are missing out.**

* * *

 **Mom's the Word**

This was kind of awkward. And considering Chess was only yesterday giving advice to God and his sister on how to build trust between each other again, that was saying something. But he had gotten used to the all-powerful beings dropping by his home for a chat. He got dropped a line via dream-message and it looked like he'd be having a visit from an angel on Sunday. And dear god (the expression, not actually him) that was kind of normal now. Visited by angels? Must be a Sunday. Chatting with Lucifer? Definitely a Monday. Counseling sessions with God and his sister? Well, that's one way to spend his hump day. But this? _This_ was weird.

For starters, there was the whole 'dead-for-33-years-and-now-back-to-life' thing. Both Sam and Dean have had their fair share of deaths and resurrections, but this was on a whole different level. 33 years! And that wasn't even the worst part.

Chess eyed the young woman before him with trepidation. Because the worst part was that she was younger than both her sons. Dean was 37. Sam, 33. And Mary? Mary was the exact age she was when she died: 29. Mary Winchester was 29 years old, and her youngest son was four years older than her. So, yes, Chess would very gladly take Lucifer over this. Because this was _weird._

"So, um…" Chess looked around the room awkwardly. Mary had her hands clasped in front of her, looking just as uncomfortable. "So, you're having trouble adjusting?"

"Well," Mary started. "It's a little weird to be younger than your sons." She paused, then said, "It's, um...just, different, y'know? When I di- uh, left, Dean was four and Sam was just a baby. And now...I mean, I don't even know them." She sighed. "It's all a little too much," she admitted softly.

"Yeah, it's a learning experience for everyone," Chess told her. "I've seen some pretty weird stuff before. I can't really say that this takes the cake because, um- well, anyway, it's still a really odd situation." He decided against bringing up the teddy bear, as much as he wanted to. Mary had enough weirdness on her plate. "Sam and Dean- this is all very strange to them too. And I know it's gonna be hard. But no matter how old they are, they're still your sons. They love you, and you love them." Oh man, he was starting to sound like an old sap.

"I know, I know," she nodded, taking a deep breath. "I get that, I really do. It's just...the other day, Dean went off with that angel friend of theirs, Cas. Sam said they went to a bar. A bar! My four year old little boy went off to a bar." She looked so sad then, shoulders slumped in defeat. "I missed their entire lives," she whispered.

"This isn't going to be easy," Chess told her. "But you _can_ do this." She didn't really look like she believed him, so he perked up a little and said, "How 'bout we work on something else while you're here?"

Mary looked up at him. "And what's that?"

"Technology," he answered, pulling out his phone. "I'm sure all the advances are confusing you, and I think learning how to use it all will help you adjust and cope better."

"I, um, I guess so." Mary looked dubious when Chess moved next to her on the couch and gave her his phone. "It's a galaxy s4," he informed her. "It's a bit of an old model, but that's fine."

"Sam gave me a phone," Mary told him. "It was an old one they had." She pulled it out of her pocket. It was _ancient._ It still flipped open. Had a full keyboard though, so that was good. It looked like they gave Mary the easiest, simplest cell they had.

"Those things are pretty old," Chess told her. He pressed the home button on his phone and the screen lit up. "See, now it's a just tap it." He demonstrated by sliding the unlock and tapping in his password. He left her to swipe through his apps while he went to get his laptop. He hoped the Winchesters didn't get mad at him for teaching their mom how to use the internet.

And hour later, Mary had a pretty good grasp on things. Chess was by no means a tech guy, but he showed her the basics and explained simple things that everyone took for granted these days. It seemed to be helping. Chess got her talking again about Sam and Dean while they worked, gently guiding her through the difficult process of getting to know her sons once more.

It was weird.

Once, several years back (and wow, he's known the Winchesters 7 years now), Chess had counseled a father and his daughter after having no contact for something like ten years. That was difficult; the girl had a lot of pent up rage towards her father, and the man just really wanted to get to know her. That was nothing alike to Chess' current situation with Mary. But it was the closest thing there was. Really though, there just really wasn't anything like having your dead mother come back to life after 33 years (and that was excluding the whole God and his sister part). So, yeah, this was really weird, and extremely difficult. Chess was really missing Lucifer by the end.

"Well, um, thanks for your help," Mary told him when their hour was up. "I know that this is all really...odd."

"Please, I was once a teddy bear doctor," Chess brushed off, though now he was thinking that this was actually weirder than the teddy bear. The fact that he found something weirder than the giant, talking, suicidal teddy bear really made him want a drink.

Shaking away uncomfortable memories, Chess asked, "Will you be back next week?"

"I'm not sure," Mary answered. "I'm not really comfortable with this...therapy stuff."

"Well, just think about it," he told her with a smile. Internally, he was weighing the odds of what Sam and Dean were paying him with if it was really worth it.

"I will," she promised. "Thanks again." And then she left. Chess went and got a drink from his kitchen. He called Jack over and vented to him over a glass of scotch, describing every supernatural thing that's happened to him since meeting the Winchesters. Damn, he really hated those boys.

-0-

"So, um...why are you here exactly?" Chess found himself asking. "You were kind of vague in the...dream message. Thing." Before him sat an angel. It was a little disconcerting, because all of Chess' experience with angels (Castiel and Lucifer) were at least adults. Or adult-looking. This guy looked like he should be in high school. College, at the most (though it was doubtful). He wore a ripped, AC/DC t-shirt, baggy jeans, a black jacket, and he even had a backpack with him. Chess assumed the kid (the actual kid the angel was using as a vessel) had it with him when he said yes. Chess was now wondering why teen-angst personified was saying yes to the voice in his head claiming to be an angel. And then he became concerned.

The angel (his name was Zadkiel) looked a little nervous. If Chess knew angels a bit better, he would know that they rarely showed emotion, and this meant that Zadkiel was actually a lot nervous. But Chess' only experiences were, again, with Castiel and Lucifer, who were kind of on opposite ends of the spectrum.

Anyway, Zadkiel was nervous. He stewed for a few moments before saying, "I have...questions." He said 'questions' as if he'd be sent right off to heaven jail just for uttering it. It actually sounded like he really meant something different, and Chess skimmed through his knowledge of angels until he landed on a word that could make them nervous: doubts. His suspicion was confirmed when Zadkiel spoke again. "Heaven has gone through a lot of changes in the last several years. And there's been so much turmoil and confusion, and-" His voice quieted. "-and a lot of deaths. And now, our father has returned- only to disappear again with the Darkness. But he told us something before we left. He told us to...well, essentially to think for ourselves a little. I wonder if he meant that we should be more like... _Castiel."_ And that was whispered, Zadkiel leaning forward a bit as if it were a secret, eyes widened with fear. It was like Castiel was now the Voldemort of heaven, no one wanted to utter his name. This really made Chess question heaven, that they were more wary of Castiel than they were of Lucifer.

Listening to Zadkiel, Chess thought he wanted advice on how to 'think for himself.' It very quickly became clear, however, that the angel never intended such a thing. Actually, all he wanted was someone to talk to about his doubts. To help him get rid of them. Wow. Angels were dense.

"So let me get this straight," Chess said, leaning forward a bit with his hands out to outline his words. "All the top angels conspire to bring about the apocalypse, ensuring the end of days. After the apocalypse ends, they try to _restart_ it, because...reasons. Then, it is discovered that an angel named Naomi is brainwashing you guys to make sure you stay in line. And you guys all hate Castiel, because he decided to protect your father's creation. And you still one hundred percent believe that heaven is always right." Chess was used to talking to Lucifer, who knew sarcasm. And also just basic common sense. Zadkiel, apparently, did not.

"Yes, that is correct," the angel told him. "How do I get rid of these doubts?" Hey, at least he was willing to use the 'D' word now! If all angels were like Zadkiel, then this was one screwed up family. Like, even more so than Chess already knew.

Chess went and grabbed a glass and the bottle of scotch before returning to an anxious looking Zadkiel. "Personally?" Chess replied while he poured himself a generous amount of alcohol into his glass. "I think the angels are seriously screwed up. And I mean that in the best way possible." That was true. The best way possible just happened to be not so great. "Seriously, just from talking to you, talking to Castiel, and talking to Lucifer, I can tell there's some major problems going on upstairs." Chess took a large gulp of his drink and winced as it burned down his throat. You really shouldn't gulp scotch. Especially when you're a lightweight like Chess was (though his recent influx of supernatural clients was quickly turning him into a regular at the bar he still worked at). "It's probably better than what it used to be, when the archangels were still trying to start the apocalypse, but still pretty messed up." Now, Chess would later blame the scotch for what he said next. Because, honestly, he should've known better. "It sounds like you all could use some therapy." And from that moment on, he was doomed.

* * *

 **Next up: Chess quits his day job**


End file.
